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N-methyl-2-pyrrolidone → N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazol-2-amine

HRID 1698562
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HRID 1698562 반응식
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:4]=2[N:3]=1.[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH2:24])=[C:22]([O:28][CH3:29])[CH:21]=1.CN1CCCC1=O>O>[Cl:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:4]=3[N:3]=2)=[C:22]([O:28][CH3:29])[CH:21]=1
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참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 672730962-Chloro-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole

생성물 1

HCID 58012305N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazol-2-amine수율 55.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
130 °C

실험 절차

A mixture of 2-chloro-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole (120 mg, 0.450 mmol), 4-chloro-2-methoxy-6-methylaniline (231 mg, 1.35 mmol) and 1-methyl-2-pyrrolidone (0.5 mL) was stirred at 130° C. for 2 days under nitrogen atmosphere. The mixture was diluted with water, extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10:1-1:1) and crystallized from iso-propanol to afford the title compound as colorless crystals (100 mg, 55%).

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10:1-1:1)
  6. customcrystallized from iso-propanol

출처 및 근거

ORD 기록
ord-c137ad9cd4474bf4940b40f6dea8cc5f
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163935B2

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